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Record Information
Version1.0
Creation Date2016-09-30 22:34:38 UTC
Update Date2020-04-22 15:04:42 UTC
MCDB ID BMDB0000669
Secondary Accession Numbers
  • BMDB00669
Metabolite Identification
Common NameOrtho-Hydroxyphenylacetic acid
DescriptionOrtho-hydroxyphenylacetic acid, also known as (O-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Ortho-hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ortho-hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. Ortho-hydroxyphenylacetic acid has been found to be associated with several diseases known as eosinophilic esophagitis and irritable bowel syndrome; also ortho-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.
Structure
Thumb
Synonyms
ValueSource
(O-Hydroxyphenyl)acetic acidChEBI
2'-Hydroxyphenylacetic acidChEBI
2-Hydroxybenzeneacetic acidChEBI
2-Hydroxyphenylacetic acidChEBI
O-Hydroxyphenylacetic acidChEBI
(O-Hydroxyphenyl)acetateGenerator
2'-HydroxyphenylacetateGenerator
2-HydroxybenzeneacetateGenerator
2-HydroxyphenylacetateGenerator
O-HydroxyphenylacetateGenerator
Ortho-hydroxyphenylacetateGenerator
(2-Hydroxyphenyl)acetateHMDB
(2-Hydroxyphenyl)acetic acidHMDB
(O-Hydroxyphenyl)-acetateHMDB
(O-Hydroxyphenyl)-acetic acidHMDB
2-HPAAHMDB
HydroxyphenylacetateHMDB
Hydroxyphenylacetic acidHMDB
O-Hydroxyphenyl acetic acidHMDB
Ortho-hydroxyphenylacetic acidMeSH
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(2-hydroxyphenyl)acetic acid
Traditional Nameo-hydroxyphenylacetic acid
CAS Registry Number614-75-5
SMILES
OC(=O)CC1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyCCVYRRGZDBSHFU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(hydroxyphenyl)acetic acids
Alternative Parents
Substituents
  • 2(hydroxyphenyl)acetic acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 - 147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility44 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.99ALOGPS
logP1.31ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000669
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012331
KNApSAcK IDNot Available
Chemspider ID11476
KEGG Compound IDC05852
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5639
PubChem Compound11970
PDB IDNot Available
ChEBI ID28478
References
Synthesis ReferenceLevine, Joseph; Eble, T. E.; Fischbach, Henry. Preparation of o-hydroxyphenylacetic acid. Journal of the American Chemical Society (1948), 70 1930.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]